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Two African-American women, Loretta Smith and Jo Ann Hardesty, are vying to become city commissioner in the nation's whitest big city

Oft-criticized for its racist history that led to a small and fragmented black community, Portland now faces an unprecedented citywide contest between two African-American women, Jo Ann Hardesty and Loretta Smith.

Both are vying to become Portland city commissioner, one of Oregon's most powerful local-government posts.

Hardesty or Smith will become the first African-American woman ever on the Portland City Council, only the third black commissioner ever and the first in more than a quarter-century. The winner will be only the ninth woman ever on the council, giving women their first-ever majority on the five-member panel.

The race could say a lot about the state of racial relations in Portland, a city where white liberal guilt remains high and interracial dialogue often is stilted. So, the Portland Tribune interviewed more than a dozen prominent African-Americans, including new and emerging leaders, to explore how this race is reverberating in their community and beyond.

No group has more at stake than Portland's African-American community, hammered by gentrification that caused the scattering of its traditional base in inner North and Northeast Portland, leading to a shrinking 6 percent share of the city's population. And no group knows these two candidates better.

One of the ways Portland's black community has been disenfranchised in the past is because City Council seats are elected citywide, not by district, said Darrell Millner, emeritus black studies professor at Portland State University. So it's ironic, Millner said, that two African-American candidates are now dueling citywide after gentrification caused the black community to be dispersed geographically and culturally.

Many black leaders, anxious to get access to the seat of power in City Hall, expressed reluctance to speak ill of either candidate, saying they were fearful of hurting their future access to City Hall or weakening the prospects of two rising leaders.

"There's so few of us, the last thing anybody wants to do is shoot somebody down, because we don't have anybody to take their place," said Baruti Artharee a Hardesty supporter who served in several high posts in state and city government and the private sector. Artharee was ousted from the city of Portland by then-Mayor Charlie Hales in 2013 after commenting suggestively in public on Smith's appearance — a comment he said was misinterpreted.

Kid gloves are off

But civility in American politics is rare in 2018, and whoever wins will get considerable political power and the economic clout that comes with it. So it's unreasonable to expect that this contest will remain above the fray and differ from other elections, even though it features two African-Americans on the same side in many community fights.

"When two people run against each other, things are going to come out that we might not like," said Margaret Carter, a veteran former state legislator who is supporting Smith.

In the opening salvo of the fall runoff on Aug.14, Smith's campaign raised questions about Hardesty's failure to get business licenses for her consulting work. Hours later, in their first head-to-head campaign forum, Smith — asked to say something nice about her opponent — replied that Hardesty was good at reinventing herself.

Both are strong-willed women, unafraid to speak their minds.

Smith, a third-generation Portlander who proudly calls herself the daughter of a boxer, spent most of her working career on the staff of Sen. Ron Wyden, D-Portland, tending to constituent service. Eight years ago, she was elected to the first of two terms as a Multnomah County commissioner.

Hardesty, who relocated here from Baltimore, served three terms in the Oregon Legislature but has made more of a name for herself as a community organizer. She helped revive the local NAACP chapter and has been a vocal critic of police brutality and racial profiling.

While many black leaders are lining up behind one of the candidates, several are declining to take a public position.

Former state lawmaker Avel Gordly reportedly offered her endorsement and political advice to both candidates.

Greg McKelvey, a young leader of the police accountability movement who favors Hardesty, nevertheless speaks highly of both candidates.

"There's just a sense of pride that we do have two incredibly qualified candidates at the top of their field who made the runoff," said McKelvey, who recently took a job in Atlanta, but promises to return to Portland.

After all, noted Fred Stewart, a real estate broker who is staying publicly neutral, this is a city that long segregated blacks into the Albina area of inner North and Northeast Portland, whose leaders publicly urged black shipyard workers to return home to the South after World War II.

"This is a very good moment for Portland, Oregon," Stewart said. "This is a very positive sign for the direction the community is going."

He and others predict high black turnout, and say the race should spur other people of color to run for office here.

Traditional leaders tilt toward Smith

Smith is garnering more endorsements from mainstream African-American community leaders, especially those who have won elected office.

"I would say the majority of the black leadership is supporting Loretta," said Bernie Foster, co-publisher of The Skanner newspaper. But his paper, which covers the black community, endorsed Hardesty.

State Sen. Lew Frederick, who supports Smith, credits her for helping constituents interface with government and other institutions, her specialty when she worked for Wyden.

She's also the one that African-Americans see more often attending church and going to funerals and weddings, said another longtime black leader.

Endorsements also can relate to expected political patronage. Many black leaders head nonprofit groups that depend on grants and other government contracts.

"If you look at people supporting her," one longtime leader said of Smith, "to a large degree it's about purse strings."

"Our community's so fragile" that endorsements can stem from the "spoils system," said James Posey, who is semi-retired from the construction industry and supports Hardesty.

"Loretta got more funding for this community than anybody in a long time," Foster noted. "I think Jo Ann is down in the trenches, dealing with community organizing."

Insider/outsider dynamic

Interviews with black leaders suggest the policy perspectives and ideologies of the two candidates may not be as important in shaping their support for one over the other as personal histories and relationships. But beyond the black electorate, ideological differences figure to be more crucial.

Several black leaders agreed the race can be compared to the Bernie Sanders-Hillary Clinton split within the Democratic Party. Hardesty, like Sanders, is more progressive, approaching the campaign as the outsider and change agent. Smith, like Clinton, is the establishment liberal, more focused on working the internal levers of power.

Several said Smith is likely to attract more support from older, longstanding black residents, and church-goers, while Hardesty is likely to attract more support from younger activists, especially those concerned about racial profiling and police brutality.

Racial issues are likely to have a high profile in this race because it features two black candidates. Both candidates promise to view issues from an "equity lens," and are generating high expectations among their future black constituents.

"We can't just say we need a black woman on City Council; what we need is racial justice," said Cameron Whitten, a young activist who is now interim executive director of the Q Center.

But it will be harder to shut off dialogue, as can sometimes occur, by playing the "race card," says one black leader, because both candidates are black.

While there will be high expectations to "lift up" the black community and provide them better access to City Hall, the winner will not succeed merely by getting the black vote. Neither blacks nor millennials who likely tilt to Hardesty provide a lot of votes in Portland, Frederick observed.

Style questions

Whoever wins is likely to be a forceful presence on the City Council.

"Both of them know that in order to be effective, you have to be confrontational, especially on the Portland City Council," Frederick said.

"They're going to have three females (on the council) and they're all strong," Foster said.

Both candidates come with blemishes on their records.

Hardesty's failure to seek business licenses for her own work, and the failure of the NAACP to file required tax and other financial reports during her term as president, suggest she doesn't always follow the rules or doesn't supervise others well.

One longtime black leader said Hardesty's "Achilles heel" can be her arrogance, which she fears could get her into trouble. While praising Hardesty's work on police accountability, that leader worries Hardesty could embolden the Antifa movement, the anarchist-influenced masked protesters who have engaged in street skirmishes with police. "I think that's a problem," she said. "That can be dangerous."

Others point to heavy turnover on Smith's staff as county commissioner as a sign that she doesn't work well with others.

At one point. her wages as county commissioner were garnished because of what the IRS said was a failure to pay more than $37,000 in state taxes on a house she sold — though the agency stopped the garnishment after Smith provided additional information saying the home was a primary residence and should not have been taxed as a rental. She also was accused of making numerous inappropriate purchases on her county purchasing card, among other alleged lapses.

If the Sanders/Clinton race dynamics play out in this race, Hardesty may have the edge in Portland, where Sanders was very popular. But she can't take the left for granted.

Teressa Raiford, leader of Don't Shoot Portland, who already has announced her own candidacy for mayor in 2020 — and who has clashed with Hardesty in the past — isn't enthralled with either of the two black candidates. "They're representative of the white political agenda," she said, likening them to the two past blacks on the City Council, Dick Bogle and Charles Jordan.

This isn't a historical election, Raiford said. "I see them as status quo candidates."

Stewart, a Portland political history buff, strongly disagrees.

Portland is the "whitest of the white" cities, making this "the most unlikely race," he said.